The proposed research is to continue and extend the investigation of cyclic aminimides as potentially cytostatic alkylating agents, an investigation started with support through the Research Grant NIH CA12816. The cyclic aminimides, typically five-membered heterocycles with at least two nitrogens, contain an ammonium nitrogen next to an imide type nitrogen (two ligands, one negative charge on the nitrogen). This arrangement provides a stable molecule, unaffected by neutral buffer. Functionalization which removes the negative charge on N-2 (or a carbonyl group conjugated to it) leads to an ammonium compound with strong alkylation powers. This activation step can be the acylation, protonation, or phosphorylation of the cyclic aminimides. It is hoped that such activation may take place in cells possessing an active metabolism, so that the alkylating (activated) substance is created in the cell in which the pharmacological action is desired. Novel cyclic aminimides are to be synthesized by cycloadditions of unsaturated compounds to dialkylaminoisocyanates, by which method six classes of such aminimides have already been made (CA12816). The chemistry of the substances is to be explored, in particular in respect to the alkylating activity after electrophilic functionalization. Samples for cytostatic testing are to be submitted to NCI, and for other pharmacological tests to Merck Sharp and Dohme (and a tripartite agreement between NIH, Merck and New Mexico State University).